Islamorada 8-Bed Penthouse with Private Pool & Ocean Views

101 Gulfview Dr, Islamorada, FL 33036

Excellent from 6 reviews
4.8/5
100% of guests recommend

No. Bed

8

No. Bathroom

6

Square

5525 sqft

Location

Florida Keys

Description

Perched in Islamorada, Villa Maxx unites two connected duplex penthouses into a sweeping 5,525 sq. ft. retreat with panoramic ocean views and eight bedrooms. Bright, open living spaces flow seamlessly to the sea through glass doors, while gourmet kitchens, a wet bar, an elevator, and high-speed Wi-Fi ensure effortless comfort for families and groups.

Designed for both relaxation and fun, the property includes a cinematic screening room, rooftop terraces, a sauna, fitness space, and a surf simulator. Step outside to enjoy balconies, sunloungers, BBQ facilities, and access to resort-style amenities including a heated shared pool, hot tub, tennis courts, and a fitness center. Beach gear is provided for easy days by the shore, and the beach is just a short walk away, along with waterfront dining. With its oceanfront atmosphere, spacious layout, and impressive range of amenities, this Islamorada penthouse retreat is a sophisticated base for an unforgettable Florida Keys escape.

Key Features

  • 8 bedrooms
  • 5 bathrooms
  • Sleeps 24 (up to 16 adults and 8 children under 6)
  • Home theater
  • Balcony with lounge area
  • Rooftop terrace with panoramic views
  • Oceanfront location
  • Two connected duplex penthouses
  • Access to resort amenities

Sleeping Arrangements

  • Suite one - Bedroom 1: King-size bed
  • Suite one - Bedroom 2: 2 queen-size beds
  • Suite one - Bedroom 3: 2 bunk beds (double/twin)
  • Suite one - Bedroom 4: King-size bed
  • Suite one - Bedroom 5: 2 sofa beds
  • Suite two - Bedroom 6: King-size bed
  • Suite two - Bedroom 7: King-size bed
  • Suite two - Bedroom 8: 2 double beds

House Rules

  • Check-in: 4:00 PM
  • Check-out: 10:00 AM
  • No smoking, No unauthorized events

Amenities

Air Conditioning
Kitchen
Parking
Pool
Wi-Fi Internet
Heated Pool
Iron
balcony
Jacuzzi
Alarm
Fully Furnished
Hair dryer
Terrace
Sauna
TV - Satellite
BBQ
Internet Connection
Garden

Villa Type

Beachfront Villa

Location

Reviews

4.8/5
Excellent
Based on 6 reviews
Excellent
5
Very Good
1
Average
0
Poor
0
Terrible
0
Jonathan Phillips

Jonathan Phillips

05/28/2026 01:02

Pure luxury

The sunset views from the patio literally left us speechless. Don't think twice, book it
Jessica Anderson

Jessica Anderson

08/18/2026 00:25

Awesome time

Having 6 bathrooms was a lifesaver for our big group getting ready in the mornings. We celebrated my husband's birthday here and everyone was blown away.
Emily Moore

Emily Moore

10/15/2026 03:42

Exceeded expectations

We felt like royalty staying here, unbelievable comfort. Definetly coming back next summer
Emily Moore

Emily Moore

09/11/2026 22:53

So relaxing

Honestly, I wasn't expecting the villa to be this spacious. The living room layout is huge and great for late night board games and drinks. Will be telling all my friends about this spot.
Anna Young

Anna Young

09/06/2026 12:18

Perfect for our group

If you are hesitating to book this place, just do it. You wont regret it. The kitchen was fully equipped, we cooked big family dinners together easily.
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6 Reviews